


Hook-Up Brothers

by Badboylover24



Series: Hazbin Shipcember Favorites [3]
Category: Hazbin Hotel (Web Series)
Genre: Cute when Blushing, F/M, Hat Blushing, Parody of matchmaker scene from pilot of Olsen Twin sitcom, Pentious & Aracknis are best friends, Pentious has a crush on Cherri, Spider Brothers play matchmakers
Language: English
Status: Completed
Published: 2020-12-15
Updated: 2020-12-15
Packaged: 2021-03-10 22:19:52
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,747
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28084572
Author URL: https://archiveofourown.org/users/Badboylover24/pseuds/Badboylover24
Summary: Here’s the 3rd Hazbin Shipcember fanfic for my next favorite ship: Cherrisnake (I support it and Pentniss).The Spider Brothers play matchmaker for their best friends to get them together.Parody of the matchmaker scene from the pilot of Two of a Kind w/the Olsen Twins.Don’t own said sitcom or Hazbin Hotel.
Relationships: Cherri Bomb/Sir Pentious (Hazbin Hotel)
Series: Hazbin Shipcember Favorites [3]
Series URL: https://archiveofourown.org/series/2040693
Kudos: 10





	Hook-Up Brothers

Cherri Bomb is Angel Dust’s best friend.

Sir Pentious is Arackniss’s best friend.

Despite these awkward facts, Angel agrees with his older brother on one thing about the two turf-war rivals since Charlie and Vaggie forced them into a truce.

“We gotta get ‘em to give each other a chance so we can hang out bettah. This tense distance is buggin’ Charlie to erasin’!” The two brothers were hanging out at their favorite café, but thinking about their best friends not wanting to socialize with each other was making their tiramisu more bitter than sweet.

“I know, Anthony,” Arackniss sighed, lighting his cigarette while his brother sipped his mocha. “But neither of ‘em wants to budge. As if Penn’s crush on her isn’t awkward enough for the situation.”

“PHHHHHHHHHT!” Angel spat out his drink in shock (they’re outdoors, by the way) before turning to his brother sharply. “WHAT?!?” Arackniss froze and dropped his cigarette when he realized what he just said.

“Please tell me I didn’t say that out loud,” he whimpered to the taller spider who only nodded in shock. The black one facepalmed with a groan.

“Lo e la mia grande bocca del cazzo…”

“How long has he been fuckin’ crushin’ on her?!” Angel demanded.

“From what he told me,” his brother answered hesitantly, “since the Princess started her redemption project. He said that he admires that fiery passion of hers ‘n’ wants to make her his queen once he ‘conquers all of Pentagram City’. I told him he could’ve just asked her to form an alliance, but he said she’s ‘not one for sharin’ turfs’.” He turned to Angel before finishing. “No offense.”

“Eh, none taken,” Angel waved it off. “He’s not wrong ‘bout that. ‘N’ now that I think ‘bout it, that would explain his wanting to be hip.”

“Ugh, don’t get me fuckin’ started,” Arackniss sighed. “He’s still tryin’ to get his slang right. Either way, I dunno what we can do about it. I mean, it’s not like we could use Penn’s crush to our advantage.”

“Maybe we can~” That’s when the smaller spider looked into Angel’s mismatching eyes and saw the gears turning in there.

“What exactly do you have in mind?” he asked suspiciously. His brother crooked a claw at him, so he leaned forward so the taller spider could whisper his little scheme into his earhole.

*~*~*

A few days later finds Cherri Bomb and Sir Pentious visiting the Hotel once again. The cyclops was reading her favorite gossip magazine on one of the lobby couches while the cobra was reading a book and drinking his tea at the bar some feet away, neither of them glancing at each other. It wasn’t long before the Spider Brothers entered the lobby and found their best friends in the same room together.

“Ya ready, Niss?” Angel whispered to his brother.

“Yeah, I remember the plan,” the shorter spider answered.

“The Operation BFF Hook-Up is a go~” He then walked over to Cherri while Arackniss went over to the bar, mouthing out “BFF Hook-Up?!” in disbelief. When he got to the bar, he hopped up onto the stool right next to Pentious.

“The usual?” Husk asked him while cleaning a shot glass behind the bar.

“Grazie,” he answered with a nod before turning to Pentious. As the feline got to preparing a tumbler of Wild Turkey, the snake glanced up at his friend to see him…staring at him. He’s just…staring…

“Is there something wrong, Niss?” Pentious finally asked before looking up at his hat while placing a hand on its side. “Is there something on my hat?”

“Sorry, Penn,” the spider answered with a shrug and a shake of his head. “It’s just…I just don’t see it.”

“Don’t see what?” Husk asked, handing him his drink.

“The fact that a genius like Penn could be too stupid to not notice Cherri Bomb has the hots for him,” the spider answered, taking a sip of his drink. Pentious scoffed indignantly.

“Arackniss, you know I don’t tolerate others—“ The snake stopped his scolding and blushed a bit at what his friend said. “Wait…Cherri Bomb…the hots for me?”

“Yup,” Arackniss answered casually.

“As in…a crush?”

“Yup.” He then glanced over at the cyclops’ direction with a smirk.

“Oop, don’t look now,” he then said to Pentious, “but she’s checking you out right now.” The two of them and Husk glanced at Cherri’s direction to see her still reading her magazine as Angel got up to her.

“Oh, she looked the other,” Arackniss sighed to the confused Pentious with annoyance. “Told ya not to look.”

Meanwhile, Angel just got to Cherri’s side with a sigh.

“Poor naïve Nissy,” he said, sitting next to her and looking at his fingernails as she turned to him with confusion. “He’s offerin’ moral support to Penn again.”

“Whacha mean, Angie?” she asked with an arched eyebrow.

“Aw, c’mon, sugah-tits,” he answered, turning to her. “It’s obvious he’s got it bad for ya now, as in a crush.”

“Edgelord’s got a crush on me?” she hissed with surprise.

“Duh,” her friend chuckled. “Why else would he be checkin’ ya out?”

“No way” she chuckled with a slight blush. “He’s not checking me out.”

“Well,” Angel explained with a casual shrug, “from what I heard from Nissy, that’s cuz he looks away whenevah ya turn to see if he is.”

Cherri’s expression softened into confusion before she turned to the bar. Sure enough, she saw Pentious staring at her a split second before he jumped with surprise and hid his face behind his book. Immediately, she understood that he’s flustered; his book’s upside down, and his Hat’s looking away with a bashful blush. 

That’s kinda…cute.

Arackniss and Husk noticed also and tried to look conspicuous; Husk with polishing his glass, and Arackniss drinking his drink.

“Omigod!” Cherri hissed, turning to Angel with a fangirl grin. “He was checking me out!”

Back at the bar, Pentious peeked over his book at Arackniss and Husk, his face now red.

“Oh, my stars,” he hissed softly. “She was checking me out!”

“See?” Arackniss said with a smirk. “You’ve a chance with her.”

“But…what should I do?!” the snake hissed, obviously freaking out.

“Well, I may be too old for this shit,” Husk answered, “but Charlie’s got this karaoke-dinner party comin’ up Friday night. Maybe you can ask her out on a date there. Tell her ya wanna get to know her better.” The snake then lowered his book with a quick glimpse at Cherri.

“Well, I do enjoy a bit of karaoke…” He then thought about it before placing his book on the bar. “Alright, I’ll do it.” He then got up from his seat to fix up his jacket and straighten his tie. And to finish it off, he licked a claw before brushing it over an eyebrow and smoothing it out. He then turned to the guys.

“How do I look?”

“Stylish,” Arackniss answered, raising his glass in approval.

“Now hurry up and ask her out already!” Husk snapped, surprising the snake.

“Alright, alright,” he replied, slithering off before muttering. “Lay off the catnip already.”

“I heard that!” Husk yelled after him as Arackniss snorted a laugh.

Meanwhile, Cherri and Angel saw Pentious slithering up to them.

“Shit, he’s coming this way,” Cherri hissed to Angel. “What should I do?!”

“Give him a chance,” Angel answered simply before getting up. “I gotta go anyway; I need to talk to Nissy.”

“Angel, wait!” But she was too late; Angel had already left. She could only sit there nervously as Pentious got up to her.

‘Okay, keep your cool. Keep your cool. Keep your cool…’

“Uh, hello, Miss Cherri…” She looked up at Pentious, who’s blushing red as was his Hat. Damn, how did she not notice sooner how cute he is when he blushes like that?

“Uh, hey,” she said, trying to not sound so nervous. “What’s up?”

Pentious meanwhile couldn’t help but notice the pink dusting her face just under her eye. Although it seems to contrast with her red eye and red tattoos, it suits her in his opinion.

‘She so cute blushing like that,’ he thought before snapping out of it and clearing his throat.

“W-Well,” he then said, “as you know, Princess Charlotte and Miss Vagatha want us to put our bitter rivalry behind us for the sake of our respective best friends.”

“Y-Yeah, they did,” she replied, feeling pretty guilty about dissing someone who offered to care for her best friend because of Valentino and Henroin.

“Well,” he then continued, “Husk told me about this karaoke-dinner party the Princess is hosting Friday night, so…I was wondering…” Cherri looked up at him with a brighter blush.

‘Is he really asking me out on a date?’

“Would you like to get to know each other better over said dinner?” Yup, he is.

Cherri immediately remembered Angel’s words.

“Give him a chance.” She figured that getting to know her rival-turned-ally wouldn’t be so bad because of Angel and Arackniss. Besides, she always did regard him as a cute steampunk kind of guy.

“Sure.” Pentious sighed sadly.

“Yes, I figured you would say n—“ He stopped with wide eyes before turning to the cyclops getting up from the sofa. “Wait, really?!” Cherri had to smile at his cute reaction.

“Yeah, it sounds like fun,” she answered before going right up to his blushing face. “And don’t worry; I don’t bite on the first date~” And she sealed that promise with a peck on the cheek, making Pentious’s hood flare up with surprise. Cherri had to hold back a giggle.

‘Damn, he’s just too adorable to say no to.’

“Welp, I see Friday night at…6 then?”

“O-Of course,” he stammered in awe, his hand on his cheek. She then waved to him with a smirk as she left.

“See ya then, Edgelord~” Pentious didn’t lash out at the nickname; he was too busy screaming internally like a fangirl.

At the bar, Angel and Arackniss watched the two of them before fist-bumping with smirks. Husk noticed this with an arched eyebrow.

“You two tricked them into this, didn’t ya?” he asked matter-of-factly.

“Damn right we did, Husky~” Angel answered, sipping his drink with a wink. The cat then sighed with a groan before grabbing himself a Bud Lite.

“I really am gettin’ too old for this shit,” he grumbled a before taking a good swig.

**Author's Note:**

> “Lo e la mia grande bocca del cazzo…” — “Me and my big fucking mouth...”
> 
> Coming up next will be ValVox. I may not be that fond of Valentino cuz of his abuse towards Angel, but I thought up a good sequel to my first fanfic. Until the 21st!


End file.
